This paper reports the results of a study that explores the relationship between farm woodland owners' stated intentions for owning woodland, and the structure and composition of these woodlands in the states of Illinois, Indiana and Iowa in the upper Midwest of the United States. Data from two sample-based inventories conducted by the USDA Forest Service, Forest Inventory and Analysis (FIA) program were combined for this analysis—the FIA forest resources inventory and the National Woodland Owner Survey (NWOS). We looked for relationships between product value and investment in woodlands, as reflected in volumes and tree quality. We also examined whether measures of diversity reflected specific management focus. Our results partially supported our hypotheses. Woodland-focused ownership reasons were found to have larger volumes and individual tree sizes. We found that a passive woodland ownership reason—that woods were “part of the farm”—generally had lower volumes per hectare. Although we were not able to differentiate between different forest product classes and measures of volume, we did find that those landowners who harvested veneer had more volume than those who harvested for firewood. Woodland owners who salvage-harvested their woodlands—a harvesting reason that is more reactive than proactive—exhibited lower volumes per hectare than those who harvested for more proactive, product-focused reasons. Biodiversity was also found to be related to the ownership focus and harvest intent. Generally, there was lower diversity in overstory species when the woodland was viewed merely as “part of the farm,” when the product harvested was fence posts and when timber was harvested for salvage or land clearing. The small sample size limits our analysis, but we can conclude that focusing the woodland owners on management of their woodlands—regardless of what the specific management goals might be—should increase productivity and biodiversity of those woodlands.